Abstract
Methyl 2-iodo-2-(phenylsulfonyl)-4-pentenoate ( 8 )is reacted with N-BOC-allylamine to afford substituted 3-azabicyclo-[3.3.0]octanes ( 10 ) in a process which involves an initial iodine atom-transfer annulation followed by an ionic cyclization. The geminal carbomethoxy and phenylsulfonyl groups are then efficiently converted to either an exocyclic olefin or to a carbonyl group. The latter transformation allows phenylsulfonylacetates to be used as surrogates for acyl radicals in synthesis.
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